Malcolm Gladwell’s Guide To Winning

by | Aug 27, 2014 | Life

Malcolm Gladwell wants me to protest at a large publishing company. “You should walk up and down outside with a sign that says they owe you money,” he says, on the phone from New York. “They’re an established, prestigious organisation. You’re a freelance writer. They’re mistreating the little man!” The company does owe me money. 
I wrote for it months ago and I am still fighting to get paid. Despite a barrage of calls and emails, 
I am apparently easy to ignore.

The small act of defiance that Gladwell 
recommends is part one of a month-long master class in how to be a successful underdog.

For the next five weeks, I’ve got the bestselling author in my corner as I take on a series of personal giants, using key lessons from Gladwell’s most recent book, David and Goliath. If I’m Rocky, he’s Mickey – my straight-talking personal trainer, guiding me through each battle with tips, inspiring stories and the pluckiest of underdog tactics.

He may not be a conventional self-help “guru” but, whether he likes it or not, his devoted followers have effectively turned him into one. Gladwell’s books – nine million in sales and counting – are about the little things that make people tick, blending armchair psychology with smart insights into business, love or happiness.
He is also a hugely popular public speaker, a high priest of the popular TEDTalks. One speech he gave on choice and contentment has been watched close to three million times online. 
Presidents quote this man.

The timing of his new book is certainly shrewd. In a post-recession economic climate, with everyone nursing the mother of financial hangovers, it’s easy to feel like an underdog. Wages are frozen, spending power is clipped, savings and pensions mean nothing and house prices are out of control. Since many people feel outmuscled in some way or other, can Gladwell’s clever insights about the world make a real difference to an average underdog like me?

Gladwell is up for the challenge – which is why I find myself contemplating a one-man picket outside a company I occasionally work for. It’s about changing the way I think about giants; you can use their size against them. Take David and Goliath. Gladwell says we shouldn’t be surprised David won, because he fought with a sling, an effective long-range weapon, whereas Goliath was expecting a hand-to-hand fight. Once it became a long-range fight, size was irrelevant.

“The point is about Goliath, not about David,” Gladwell says. “We misperceive Goliath, because we don’t look beyond his size and we don’t 
understand that the very thing that makes him 
so terrifying to us is the source of his vulnerability. What looks like an advantage is actually 
a disadvantage.”

So when it comes to my battle with the publishing company, the fact that they’re a large organisation and I’m a one-man army should form the basis of my tactics. “You should shame them,” says Gladwell. “Do something disagreeable, something that shocks them a little.”

Choose Small

A little everyday insurgency is not a bad idea. It’s a proven strategy in the digital age, where social media can empower anybody. My fellow underdog, Jim Boyden, posted a broadband bill on Facebook after his deceased father-in-law was fined for late payment. He received a public 
apology. Andrew Sharman, a little-guy web 
designer, blogged his way to a refund for a 
crap package holiday.

Gladwell thinks I should go traditional. It’s a liberal, campaigning magazine that owes me money; they’re supposed to be on the side of the little guy. Picketing them will highlight their hypocrisy. I feel a righteous buzz from the idea and tell Gladwell I’ll do it. It could work, but the stunt also makes me nervous. An underdog shouldn’t have to burn bridges or risk his career just to chalk up a victory. I decide that I need more evidence. So, while I think about potentially painting a placard, 
I line up my next Goliath – fat.

Fight Dirty
You can’t beat Goliath if you play by his rules. 
A shepherd would be pummelled if he engaged 
a giant warrior in hand-to-hand combat. A complaint from a writer is easily ignored by a big company. This is Gladwell’s next lesson: when you face Goliath, use shock tactics. David won 
because he used a sling; insurgent armies have long frustrated bigger enemies by using 
unconventional guerrilla tactics.

I’ve decided to go guerrilla on my gut. For years I have been trying to lose weight. Fad diets don’t work. Each time I fall off the diet industry’s wagon-of-the-month, everyone says the same thing – nutritionists, GPs, my wife: don’t do anything drastic, eat smaller portions, more vegetables, less sugar. But guess what? I can’t do that. As soon as I start eating, my next meal is calling. Once I start, I want to binge. Small adjustments don’t work. I eat all or nothing.

So for the next month, I’ll eat nothing. Ignoring conventional diet-industry mantra, everything from Atkins to the vegetarians, I found research which suggests that fasting every other day is good for you. It’s controversial, but not only does it promise that you’ll live longer, one study also found that crash diets help you lose more weight long term than the steady approach. Done: for three days a week I will fast. I know it can work because I did it 10 years ago – the last time I was slim. It was hard, but it was also the thinnest (and happiest) time of my life.

I tell my underdog PT. “That’s kind of extreme,” says Gladwell, approvingly, “which is the whole point. People who have nothing to lose are willing to follow extreme strategies. If you feel like nothing else works for you, then an unexpected strategy becomes a legitimate choice. Not eating for three days will certainly lose you weight. Whether you’ll keep it off is another matter, but it is a real 
hard-ass Lawrence of Arabia strategy.”

It is hard-ass – like the 5:2 diet but, well, much firmer of buttock. I don’t seek anyone else’s 
opinion. It’s about what works for me. So I start not eating every other day. I do, however, give up on protesting outside the company that owes me money. When I tell Gladwell about fasting, he says that you can resort to extreme tactics when you feel you have no other option. But I don’t feel that way about the money I’m owed. To protest, I would have to buy a ticket to another city, which would cost me more than I can comfortably spend on a statement. I could also be ignored and left looking silly. Even though I chicken out, after a few more emails, the company pays me and offers a 
late-payment fee, which seems a hollow victory.

By the end of week one, my underdog lifestyle feels like an ultra marathon. On fasting days, I’m tired, dizzy and grouchy. There’s a metallic taste in my mouth. But I look forward to the next day’s breakfast and can exercise later in the evening because I’m not stuffed with food. I allow myself a milky coffee and sometimes I slip up and eat my two-year-old son’s leftover sandwich crusts. Even so, I lose an impressive 1.8 kilograms without reading a diet book or picking up any items labelled “low-fat”. If I’m winning, it’s because I’m doing it my way.

Aim Low, Win Big

With slightly looser jeans, I’m confident going into the third experiment, an attempt to advance my career by securing new, lucrative clients. It stems from Gladwell’s discussion of whether it’s better being a big fish in a little pond or a little fish in a big pond. The example he uses is French Impressionist painters such as Monet and Renoir. In the 1860s they were broke. They wanted to see their paintings in an elite exhibition, the Salon, but to be accepted they would have to change their style. They debated starting their own exhibition instead. Should they be little fish in a big pond or big fish in a little pond? They chose the latter and became recognised as great artists.

“Prestige is a two-edged sword,” my guru 
tells me. “Trying to get into some place that’s 
selective and prestigious is a mixed blessing. We focus too much on the advantages and too little on the disadvantages.” My own Salon is the publishing industry of New York – a much bigger, more 
lucrative market than I’ve experienced. I’ve spent time writing to publishers in New York and never had so much as a rejection. It is a very big pond and I’m a very small fish.

Gladwell thinks I stand a better chance of long-term success by starting in a small pond. I see what he means – an average student can dominate in a less prestigious university; no one starts out at the top. “That’s the strategy I took at the beginning of my career,” says Gladwell. “I wanted to be a big fish in a little pond. I thought I would have a better way of making myself known down the road.”

I stop pitching to the big newspapers and magazines (who ignore me anyway) and try smaller blogs and websites instead. Silence. I don’t hear anything for a week and email Gladwell to tell him it’s not working. I’m having as much success as 
I did with the major publications. He replies: 
“I suspect you’re being modest – if you can write for Men’s Health, you can certainly write for a blog. Either that, or the blogs are practising a kind of 
self-defeating snobbery.”

Maybe they are. Maybe I should keep trying. Except, what good will it do if my pond is so small that nobody even notices? I’m not convinced an underdog can succeed by proving himself in a puddle. The establishment may see prodigies like Gladwell (he went to university at 16) and invite him into the big pond, but would they take a risk on an underdog like me? I think underdogs need to force their way into the establishment. For most underdogs making a splash in the big pond is essential. Gladwell disagrees.

“If you’re a brilliant person, it doesn’t matter what school you go to,” he says.“If you’re a dumb person it doesn’t matter either, because you’re dumb or lazy. People are constantly confusing these things. Smaller institutions can give people far more 
freedom or the chance to pursue things that they might not have been able to do.” Another email arrives. It’s from one of the New York websites that I’d pitched to – has the small pond invited me in? Sadly not: they decline my idea and I shut down the computer feeling very much the underdog.

On the upside, my kamikaze diet strategy is working. I fit into my clothes and my rings come off more easily. It’s been four weeks and I’ve lost just over six kilos. On eating days, I gorge less because my stomach has shrunk. If I do binge, it’s not as much. My appetite is under my control and the diet industry had nothing to do with it. My confidence is returning just in time for my final experiment.

The Sharp End

What Gladwell has been drumming into me is that advantages and disadvantages are often misconstrued. The most confusing examples are called “desirable difficulties” (see below). These are trials that inflict an underdog, which we assume would hamper their success, but which actually turn them into winners. As Gladwell puts it, “Making someone’s life a little more difficult can be highly advantageous.” He notes that people coping with dyslexia gain advantages, such as listening better than their peers do. Likewise, an unemployed person has the time to work on their dream business plan.

The little guy can succeed thanks to so-called “desirable difficulties”, traits that look like burdens but which can be vital to beating the odds:

Master your skills
Whatever your game, practise in a small space. Play tennis in one half of the court or practise free kicks from far out. Psychologist Robert Bjork says that forcing your brain to respond to variation “engages the very processes that support learning.” In other words, you improve – fast.
Beat your handicap
“On a golf course, mix up the order you use your clubs,” says Bjork. This creates a sense of difficulty and slow progress, but your handicap will improve faster.

Save your memory
When prepping a 
presentation or speech, print it out in a font that’s hard to read. You’ll remember more of it because you have to concentrate harder, says a Prince-ton University study.
Defeat fat for good
Impose a strict deadline. If you want to lose weight for a holiday, give yourself until two weeks before you fly to make the weight. You’ll work harder and be extra strict with nutrition.
Be more creative
Ditch the keyboard and brainstorm ideas for a project by making detailed hand-written notes. It takes longer but you’ll come up with better ideas.

But since I don’t have any desirable difficulties, I need to manufacture my own. In other words, to fix my final big problem – motivation – I need to turn myself into an underdog. Here’s the problem: I waste time. When I have work to do, I make coffee, watch television, go for runs and avoid working. I’m going to try to fix this by giving myself less time. Instead of declining jobs when I don’t have the time, I shall accept all work offers. I’ll intentionally take on too much work. I ask Gladwell if he thinks it will work. “I have no idea,” he says. “The thing about desirable difficulties is they are high-stakes strategies. They produce failures as well as lots of real winners.”

It quickly becomes a nightmare. I say yes to work I have no time for. I say yes to work that requires travel. I have so much work that I’m panicking. I work late and start early. And did I mention that I’m really, really hungry? Even so, I stop making coffee. I watch no TV. On the fifth day it dawns on me that this is good – it’s working – because I’m getting the work done, even if I stress out, snap at my family and cancel social plans. It’s a victory of sorts – I’ve given myself a difficulty, made myself an underdog, and it’s forced me to work hard.

That’s been something of a theme for the past month. My experiments have proved that if an 
underdog is going to have his day, he has to 
be up for a scrap. My attempt to use a large 
company’s size against it faltered because I was too nervous of its size in the first place. I’m astonished at how much weight I’ve lost, but going without food on three days a week is hell. My attempt to expand my career options by aiming lower has yet to pay off. And the path I took to a more efficient workflow left me stressed.

Not that I feel beaten; it’s been strangely empowering being an underdog. I can’t think of a fight I would now feel cowed by. I don’t feel so helpless when I’ve been wronged by a large company. I have kept the weight off and at work, I’m busy, productive and earning more money than I have in months. None of that feels like an underdog’s experience.

Learn more about Gladwell’s book, 
David and Goliath by visiting

By Andrew Hankinson

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